PodcastsComedyUncomfortable Conversations with Josh Szeps

Uncomfortable Conversations with Josh Szeps

Josh Szeps
Uncomfortable Conversations with Josh Szeps
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425 episodes

  • Uncomfortable Conversations with Josh Szeps

    Violent Clashes at Israeli President's Bondi Visit

    12/2/2026 | 53 mins.
    Violence erupted this week as police in downtown Sydney clashed with thousands of activists protesting a visit to Australia by the Israeli President, Isaac Herzog. He was invited to Australia in the wake of the anti-Semitic Bondi terrorist attack.

    In his weekly livestream, ‘Josh vs the News’, Josh sits down to sift through the media reporting and how we might best think about protest, free speech and Palestine.
  • Uncomfortable Conversations with Josh Szeps

    Fmr John Oliver Writer on Bias, Blackface & Making Sense of the News

    09/2/2026 | 1h 56 mins.
    Has our culture had a grown-up conversation yet about race and gender? Or did the media flip from the casual bigotry of the 20th century to the censorious hysteria of the 2010s in a way that empowered the rise of the New Right? And what was it like to work as a comedy writer on a hit progressive comedy show as the culture underwent The Great Awokening?

    Jeff Maurer was a writer on Last Week Tonight with John Oliver for its first six seasons. He left in 2020 after feeling its editorial angle had become too ideologically captured. Now, Jeff has a wildly popular political-satire Substack, “I Might Be Wrong”.

    Josh intended to chat with Jeff to help make sense of Minneapolis, Epstein, ICE, the 2020 election ballots, Don Lemon’s arrest and, of course, the Melania documentary. There’s been a lot, lately. But this conversation evolved into a far more fascinating and funny discussion about what the controversies over blackface and transgenderism can teach us about how the media lost its way; about whether we’ve lost the ability to cover the news - and to satirise it - without preaching to the choir.

    Follow Jeff’s comedy writing below at www.imightbewrong.org
  • Uncomfortable Conversations with Josh Szeps

    Just Josh: America on the Brink

    05/2/2026 | 1h 33 mins.
    Minneapolis. ICE. The arrest of journalists. The indictment of political opponents. The pursuit of election officials. The killing of protestors.

    Is the U.S. government openly pursuing authoritarian rule? What is the risk of a low-grade, neighbour-against-neighbour spate of Balkan-style violence? How do we stitch American democracy back together? How does the Trump Administration end?

    Take this opportunity to step back from the fire-hose of news and join Josh, as he puts America's current crisis in context, homes in on the real threat, and identifies a path to national sanity.
  • Uncomfortable Conversations with Josh Szeps

    Don Lemon Arrested: Trump, ICE & the Prosecution of the Press

    02/2/2026 | 1h 24 mins.
    With the arrest of the high-profile journalist Don Lemon, the protests in Minnesota have become the new frontline of press freedom.

    Is the Trump Administration openly hunting down journalists now? Or, in the aftermath of Snowden, Manning & Assange, is Trump just more shameless in cracking down on voices he disapproves of? What happens to a democracy when reporters and commentators are targeted in politically-motivated, trumped-up prosecutions?

    Seth Stern is a civil liberties lawyer and the chief of advocacy at Freedom of the Press Foundation. He joins Josh to discuss the case against Don Lemon, the weaponisation of espionage laws, the difference between ethical journalism and genuine national-security threats, how the Trump Administration - using Minneapolis as a pretext - is criminalising the freedom of the press, and how we might fix it.
  • Uncomfortable Conversations with Josh Szeps

    An Anti-Zionist & a Pro-Zionist on “Apartheid Violence” in the West Bank

    29/1/2026 | 2h 45 mins.
    Does Israel’s military occupation of the West Bank call into question its legitimacy as a state? Or is the occupation a necessary evil to defuse the threat of an intractably hostile Palestinian population?

    While everyone's been focused on Gaza, the larger, more populous chunk of Palestine - the West Bank - has seen a dramatic escalation of violence by Israeli settlers against Palestinian civilians. Why?

    Without answering that question, no solution in Gaza will amount to a hill of beans. In this double-feature episode, Josh speaks with two people who have each lived and worked in the occupied West Bank and emerged with very different opinions. 

    Andrey X is an anti-Zionist Russian-Israeli journalist and activist who documents Israeli violence in the West Bank for his nearly 400,000 Instagram followers. Charlotte Korchack is an American-Israeli educator of Jewish & Israeli history. Both have lived in the occupied territories and reported on Israeli settlers and Palestinian residents alike.

    Josh speaks with Andrey and then Charlotte about the reality on the ground and the history & future of all the territory between the river and the sea.

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About Uncomfortable Conversations with Josh Szeps

The world has never been more connected. Yet never more divided. We yell at each other from inside our echo chambers. But change doesn’t happen inside an echo chamber. It’s time to get out, to stretch our legs, to step on some land mines. It's time to have an uncomfortable conversation with Josh Szeps. A DM Podcast  
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